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Please login to access the full content or check if you have access via2.3.2.2.1.2 Asymmetric Michael Addition of tert-Butyl 2-(1-Naphthyl)-4,5-dihydrooxazole-4-carboxylate to Ethyl Acrylate
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DOI:
10.1055/sos-SD-205-00387
Shirakawa, S.; Maruoka, K., Science of Synthesis: Asymmetric Organocatalysis, (2012) 2, 576.
A highly enantioselective synthesis of a potent metabotropic receptor ligand, (S)-α-(hydroxymethyl)glutamic acid (77), has been accomplished by the catalytic Michael addition of the tert-butyl ester 75 to ethyl acrylate, using the phosphazene base 74 (BEMP) in dichloromethane at −60 °C in the presence of the chiral quaternary ammonium salt (S,S)-3 (R1 = 3,4,5-F3C6H2). Acid hydrolysis of the resulting intermediate 76 gives the target (Scheme 34).[62]
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References
| [62] | Mee, M.-M.; Mee, M.; Mee, M.-M.; Meeee, M.-M.; Mee, M.-M.; Mee, M.-M.; Mee, M.; Me, M.-M.; Mee, M.-e.; Meee, M.-e., Mee. Meee., (8888) 8, 8888. |
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